29 Movies Every Entrepreneur Should Watch

The Social Network (2010)

On a fall night in 2003, Harvard undergrad and computer programming genius Mark Zuckerberg sits down at his computer and heatedly begins working on a new idea. In a fury of blogging and programming, what begins in his dorm room soon becomes a global social network and a revolution in communication. A mere six years and 500 million friends later, Mark Zuckerberg is the youngest billionaire in history… but for this entrepreneur, success leads to both personal and legal complications.

Directed by David Fincherm the film is based on the 2009 book The Accidental Billionaires by Ben Mezrich. It stars Jesse Eisenberg as Facebook founder Mark Zuckerberg, with Andrew Garfield as Eduardo Saverin, Justin Timberlake as Sean Parker, Armie Hammer as Cameron and Tyler Winklevoss, and Max Minghella as Divya Narendra.

Why it’s one of the best movies for entrepreneurs: The Social Network offers a riveting depiction of the contentious founding of Facebook, exploring themes of ambition, betrayal, and legal drama while providing insight into the entrepreneurial journey of Mark Zuckerberg. Through its compelling narrative and stellar performances, the film provides a captivating glimpse into the creation and subsequent controversies surrounding one of the most influential social media platforms in history.

Jerry Maguire (1996)

Jerry Maguire was inspired by an experience the sports agent Leigh Steinberg, a technical consultant for the film, had with the client Tim McDonald during the 1993 NFL season when free agency was introduced. The film was also partly inspired by a 28-page memo written at Disney in 1991 by Jeffrey Katzenberg.

Written and directed by Cameron Crowe and stars Tom Cruise as the sports agent Jerry Maguire, alongside Cuba Gooding Jr., Renée Zellweger, Kelly Preston, Jerry O’Connell, Jay Mohr, Bonnie Hunt, and Regina King. Jerry Maguire gained a cult following and has spawned several catchphrases into popular culture, such as “Show me the money!” and “You had me at ‘Hello'”, “You complete me”, and “Help me help you”.

Why it’s one of the best movies for entrepreneurs: “Jerry Maguire” provides valuable insights into the entrepreneurial journey. The film highlights key themes such as integrity, perseverance, and the importance of building genuine relationships in business.

The Pursuit of Happyness (2006)

Biographical drama film directed by Gabriele Muccino and starring Will Smith as Chris Gardner, a homeless salesman. Smith’s son Jaden Smith co-stars, making his film debut as Gardner’s son, Christopher Jr. The screenplay by Steven Conrad is based on the best-selling 2006 memoir of the same name written by Gardner with Quincy Troupe. It is based on Gardner’s nearly one-year struggle being homeless. The unusual spelling of the film’s title comes from a mural that Gardner sees on the wall outside the daycare facility his son attended. The movie is set in San Francisco in 1981.

Why it’s one of the best movies for entrepreneurs: It offers a powerful portrayal of the entrepreneurial spirit and the journey to success. The film underscores important entrepreneurial lessons, such as the importance of perseverance, seizing opportunities, taking calculated risks, maintaining a positive attitude, and never giving up on one’s dreams.

The Big Short (2015)

Based on the 2010 book The Big Short: Inside the Doomsday Machine by Michael Lewis shows how the 2007–2008 financial crisis was triggered by the United States housing bubble. The film stars Christian Bale, Steve Carell, Ryan Gosling, and Brad Pitt, with John Magaro, Finn Wittrock, Hamish Linklater, Rafe Spall, Jeremy Strong, and Marisa Tomei in supporting roles.

Why it’s one of the best movies for entrepreneurs: ‘The Big Short’ provides valuable insights into financial markets, risk assessment & management, learning from mistakes, recognizing opportunities, and ethical considerations, offering entrepreneurs valuable lessons in navigating complex and dynamic business environments.

Moneyball (2011)

Biographical sports drama film directed by Bennett Miller, based on the 2003 nonfiction book, Moneyball: The Art of Winning an Unfair Game by Michael Lewis. The book is an account of the Oakland Athletics baseball team’s 2002 season and their general manager Billy Beane’s attempts to assemble a competitive team. In the film, Beane (Brad Pitt) and assistant general manager Peter Brand (Jonah Hill), faced with the franchise’s limited budget for players, build a team of undervalued talent by taking a sophisticated sabermetric approach to scouting and analyzing players. Philip Seymour Hoffman also stars as Art Howe.

Why it’s one of the best movies for entrepreneurs: “Moneyball” is about the importance of embracing innovative strategies and thinking outside the box to achieve success, even in the faced setbacks and criticism but remaining committed to the vision. Billy Beane’s willingness to challenge conventional wisdom and adopt a data-driven approach to player evaluation revolutionized the game of baseball, demonstrating the power of analytics in decision-making and highlighting the value of teamwork and collaboration.

Joy (2015)

Based on a real-life entrepreneur and self-made millionaire Joy Mangano, who created her own business empire. Directed by David O. Russell and starring Jennifer Lawrence as Joy Mangano.

Why it’s an inspiring movies for entrepreneurs: “Joy” is considered one of the best movies for entrepreneurs because it provides a compelling narrative of resilience, determination, and entrepreneurial spirit. Joy Mangano’s journey from a struggling single mother to a successful businesswoman showcases the challenges and triumphs of entrepreneurship. The film highlights key entrepreneurial lessons such as the importance of perseverance, innovation, and overcoming obstacles. Joy’s ability to navigate setbacks, negotiate deals, and ultimately succeed in bringing her invention to market serves as an inspiring example for aspiring entrepreneurs. Additionally, the film explores themes of family support, personal growth, and the pursuit of one’s dreams, making it a valuable source of motivation and inspiration for entrepreneurs.

The Founder (2016)

Another inspiring biographical drama film directed by John Lee Hancock and written by Robert Siegel. Starring Michael Keaton as businessman Ray Kroc, the film depicts the story of his creation of the McDonald’s fast-food restaurant chain, which eventually involved forcing out the company’s original founders to take control with conniving ruthlessness. Nick Offerman and John Carroll Lynch co-star as McDonald’s founders Richard and Maurice McDonald, alongside Linda Cardellini as Ray Kroc’s third wife Joan Smith, and B. J. Novak as McDonald’s president and chief executive Harry J. Sonneborn.

Why it’s one of the best movies for entrepreneurs: ‘The Founder’ showcases several valuable lessons. Firstly, the importance of recognizing opportunities where others may not see them, as Ray Kroc did when he observed the efficiency and popularity of McDonald’s. Secondly, perseverance and determination are key traits for success, as Kroc faced numerous setbacks and challenges but continued to pursue his vision. Additionally, the film highlights the significance of innovative business strategies, such as Kroc’s idea to franchise to middle-class investors and focus on real estate as a revenue stream. However, it also serves as a cautionary tale about the ethics of business practices, as Kroc’s actions towards the McDonald brothers demonstrate the potential consequences of prioritizing personal gain over integrity and loyalty.

Wall Street (1987)

It tells the story of Bud Fox (Charlie Sheen), a young stockbroker who becomes involved with Gordon Gekko (Michael Douglas), a wealthy, unscrupulous corporate raider.

Why it’s one of the best movies for entrepreneurs: “Wall Street” portrayal of the high-stakes world of finance and the ethical dilemmas faced by those involved. It offers valuable insights into the complexities of the financial industry and the consequences of unethical behavior, making it a thought-provoking and relevant watch for entrepreneurs.

Erin Brockovich (2000)

The film is a dramatization of the true story of an American paralegal, consumer advocate, and environmental activist Erin Brockovich, portrayed by Julia Roberts, who initiated a legal case against the Pacific Gas and Electric Company over its culpability for the Hinkley groundwater contamination incident.

The film received five nominations at the 73rd Academy Awards, including Best Picture, Best Director for Soderbergh, Best Original Screenplay for Grant, Best Actress for Roberts (which she won), and Best Supporting Actor for Albert Finney.

Why it’s an inspiring movie for entrepreneurs: “Erin Brockovich” is an inspiring story for entrepreneurs, showcasing the power of determination, empathy, and resourcefulness in achieving justice and making a meaningful impact. Erin’s journey highlights the importance of standing up for what is right, even in the face of adversity and using one’s skills and abilities to advocate for those in need.

Pirates of Silicon Valley (1999)

Directed by Martyn Burke and stars Noah Wyle as Steve Jobs and Anthony Michael Hall as Bill Gates. Spanning the years 1971–1997 and based on Paul Freiberger and Michael Swaine’s 1984 book Fire in the Valley: The Making of the Personal Computer, it explores the impact that the rivalry between Jobs (Apple Computer) and Gates (Microsoft) had on the development of the personal computer. The film premiered on TNT on June 20, 1999.

Why it’s one of the best movies for entrepreneurs: Pirates focuses on the heated personal rivalry between Steve Jobs of Apple and Bill Gates of Microsoft, recounting the parallel and often intertwined stories of the two companies and their tempestuous founders.

The Wolf of Wall Street (2013)

Directed by Martin Scorsese and written by Terence Winter, based on Jordan Belfort’s 2007 memoir of the same name. It recounts Belfort’s career as a stockbroker in New York City and how his firm, Stratton Oakmont, engaged in rampant corruption and fraud on Wall Street, leading to his downfall. The film stars Leonardo DiCaprio as Belfort, Jonah Hill as his business partner and friend, Donnie Azoff, Margot Robbie as his second wife, Naomi Lapaglia, Matthew McConaughey as his mentor and former boss Mark Hanna, and Kyle Chandler as FBI agent Patrick Denham.

Why it’s one of the best movies for entrepreneurs: “The Wolf of Wall Street,” highlights the importance of ethical business practices and integrity in entrepreneurship. Jordan Belfort’s unethical and illegal activities ultimately led to his downfall and imprisonment, demonstrating the severe consequences of disregarding legal and moral boundaries in pursuit of success. It also emphasizes the dangers of excessive ambition and greed.

Steve Jobs (2015)

The film covers fourteen years in the life of an American businessman, inventor, and investor best known for co-founding the technology giant Apple Inc. Steve Jobs, specifically ahead of three press conferences he gave during that time – the formal unveiling of the Macintosh 128K on January 24, 1984; the unveiling of the NeXT Computer on October 12, 1988; and the unveiling of the iMac G3 on May 6, 1998. Jobs is portrayed by Michael Fassbender. Directed by Danny Boyle, it was adapted from the 2011 biography by Walter Isaacson and interviews conducted by Sorkin.

Why it’s one of the best movies for entrepreneurs: ‘”Steve Jobs’ emphasizes the value of perseverance and resilience in the face of adversity, as Jobs navigates the ups and downs of his career while striving to achieve his vision. Throughout the film, Steve Jobs grapples with personal and professional challenges, including strained relationships and failed projects. However, he learns to confront his past behavior and reconcile with those he has wronged, ultimately leading to personal growth and redemption.

You’ve Got Mail (1998)

Inspired by the 1937 Hungarian play Parfumerie by Miklós László (which had earlier been adapted in 1940 as The Shop Around the Corner and in 1949 as In the Good Old Summertime). It tells the story of two people (Tom Hanks as Joe Fox and Meg Ryan as Kathleen Kelly) in an online romance who are unaware they are also business rivals. The film takes its name from the greeting AOL users receive when they get a new e-mail.

Why it’s one of the best movies for entrepreneurs: ‘You’ve Got Mail’ highlights the challenges faced by small businesses when competing against larger, more technologically advanced competitors. It underscores the importance of adaptability and innovation in entrepreneurship, as seen in Kathleen’s journey to transform her business and Joe’s realization of the value of personal connections over corporate dominance. Additionally, the movie emphasizes the significance of authenticity and genuine human interaction in business relationships, showing how these qualities can ultimately lead to success, both personally and professionally.

Office Space (1999)

Satirical black comedy film written and directed by Mike Judge and stars Ron Livingston, Jennifer Aniston, Gary Cole, Stephen Root, David Herman, Ajay Naidu, and Diedrich Bader. It satirizes the work life of a typical 1990s software company, focusing on a handful of individuals weary of their jobs.

Why it’s one of the best movies for entrepreneurs: It highlights the importance of workplace culture and employee morale. The film demonstrates how a toxic work environment, characterized by micromanagement, lack of appreciation, and mistreatment of employees, can lead to widespread dissatisfaction and even rebellion.

The Intern (2015)

It follows a 70-year-old widower (Robert De Niro) who becomes a senior intern at a fashion website, where he forms an unlikely friendship with the company’s workaholic CEO (Anne Hathaway).

Why it’s one of the best movies for entrepreneurs: ‘The Intern’ is about the importance of mentorship, adaptability, and maintaining a healthy work-life balance. Ben Whittaker’s role as a senior intern highlights the value of experience and wisdom in guiding and supporting younger colleagues. His ability to adapt to new technology and work environments demonstrates the importance of lifelong learning and staying relevant in a rapidly changing business landscape. Additionally, Jules Ostin’s journey emphasizes the significance of prioritizing personal well-being and relationships alongside professional success, showcasing the need for entrepreneurs to find a balance between work and personal life to achieve fulfillment and happiness.

The Devil Wears Prada (2006)

Based on the 2003 novel by Lauren Weisberger. Meryl Streep stars as Miranda Priestly, a powerful fashion magazine editor, with Anne Hathaway as Andrea “Andy” Sachs, a college graduate who goes to New York City and lands a job as Priestly’s co-assistant. Emily Blunt and Stanley Tucci co-star as co-assistant Emily Charlton and art director Nigel Kipling, respectively. Simon Baker and Adrian Grenier play pivotal supporting roles.

The film, despite its setting in the fashion world and references to well-known figures, saw few designers and fashion personalities appearing as themselves, possibly due to concerns about displeasing US Vogue editor Anna Wintour, who is thought to have inspired a character. However, numerous designers permitted their clothing and accessories to be featured, making it one of the most expensive costume films.

Why it’s one of the best movies for entrepreneurs: Its insightful portrayal of navigating the corporate world, resilience in the face of adversity, and the importance of personal growth and ambition.

Startup.com (2001)

Documentary film directed by Jehane Noujaim and Chris Hegedus. It follows the dot-com start-up govWorks.com, which raised $60 million in funding from Hearst Interactive Media, KKR, the New York Investment Fund, and Sapient.

The startup did not survive, but it became a reference for lessons learned, as it was the subject of a 2001 documentary that follows govWorks founders Kaleil Isaza Tuzman and Tom Herman from 1999 to 2000, as the Internet bubble was bursting.

Why it’s one of the best movies for entrepreneurs: It shows the importance of understanding market dynamics and recognizing potential challenges, particularly during periods of economic instability such as the bursting of the Internet bubble. It serves as a valuable case study for aspiring entrepreneurs, offering insights into the factors contributing to both success and failure in the startup ecosystem.

Boiler Room (2000)

Written and directed by Ben Younger and starring Giovanni Ribisi, Vin Diesel, Nia Long, Ben Affleck, Nicky Katt, Scott Caan, Tom Everett Scott, Ron Rifkin, and Jamie Kennedy. The film was conceived when screenwriter Ben Younger interviewed for a job at brokerage firm Sterling Foster. Younger said, “I walked in and immediately realized, ‘This is my movie.’ I mean, you see these kids and know something is going on.”

Why it’s one of the best movies for entrepreneurs: “Boiler Room” highlights the importance of ethical conduct, integrity, and accountability in business. The film’s portrayal of Seth Davis’s involvement with J. T. Marlin serves as a cautionary tale about the dangers of prioritizing personal gain over ethical considerations, emphasizing the need to own up to mistakes and work towards rectifying them.

The Aviator (2004)

Based on the 1993 non-fiction book Howard Hughes: The Secret Life by Charles Higham, the film depicts the life of Howard Hughes (Leonardo DiCaprio), an aviation pioneer and director of the film Hell’s Angels. The film portrays his life from 1927 to 1947 during which time Hughes became a successful film producer and an aviation magnate while simultaneously growing more unstable due to severe obsessive–compulsive disorder (OCD).

Why it’s one of the best movies for entrepreneurs: “The Aviator” serves as a reminder that while ambition and innovation are crucial for entrepreneurial success, maintaining balance and self-care are equally essential for long-term fulfillment and sustainability.

Margin Call (2011)

A respected financial company is downsizing, and one of the victims is the risk management division head, who was working on a major analysis just when he was let go. His protégé completes the study late into the night, then frantically calls his colleagues in about the company’s financial disaster he has discovered. What follows is a long night of panicked double-checking and double-dealing as the senior management prepares to do whatever it takes to mitigate the coming debacle even as the handful of conscientious comrades find themselves dragged along into the unethical abyss.

Why it’s one of the best movies for entrepreneurs: “Margin Call” highlights the significance of effective leadership during times of crisis. Entrepreneurs can learn from characters like Sam Rogers, who demonstrates resilience, empathy, and accountability in guiding his team through challenging circumstances while upholding their professional and ethical responsibilities. Overall, the film serves as a cautionary tale and prompts entrepreneurs to consider the broader implications of their actions on stakeholders and society as a whole.

Glengarry Glen Ross (1992)

Based on his 1984 Pulitzer Prize–winning play of the same name. The film depicts two days in the lives of four real estate salesmen, and their increasing desperation when the corporate office sends a motivational trainer to threaten them that all but the top two salesmen will be fired within one week.

Why it’s one of the best movies for entrepreneurs: “Glengarry Glen Ross” portrays the ruthless environment of a real estate sales office, where deceitful tactics and backstabbing are commonplace. However, it also highlights the downfall of characters who prioritize personal gain over moral principles, such as Shelley Levene’s desperation leading to unethical behavior and Richard Roma’s manipulation of clients. The consequences of dishonesty and betrayal ultimately lead to the demise of these characters’ careers and relationships. Entrepreneurs can take away the lesson that success built on deceit is fleeting, and long-term success is rooted in honesty, integrity, and ethical business practices.

Baby Boom (1987)

Female-centric entrepreneur rom-com drama film directed by Charles Shyer, stars Diane Keaton as a yuppie who discovers that a long-lost cousin has died, leaving her a fourteen-month-old baby girl as inheritance.

Why it’s one of the best movies for entrepreneurs: ‘Baby Boom’ highlights the importance of adaptability and flexibility in navigating unexpected challenges, as J.C. Wiatt transforms from a high-powered corporate executive to a successful entrepreneur and mother. Additionally, the film showcases the potential for entrepreneurship to provide both financial success and personal fulfillment, as J.C. finds happiness and fulfillment as a mother and CEO of her own company.

Fight Club (1999)

Based on the 1996 novel of the same name by Chuck Palahniuk. Edward Norton plays the unnamed narrator, who is discontented with his white-collar job. He forms a “fight club” with soap salesman Tyler Durden (Brad Pitt) and becomes embroiled in a relationship with an impoverished but beguilingly attractive woman, Marla Singer (Helena Bonham Carter).

Why it’s one of the best movies for entrepreneurs: “Fight Club” provides a thought-provoking narrative that challenges conventional notions of success, encourages risk-taking and innovation, and underscores the importance of ethical leadership and personal growth in entrepreneurship.

Chef (2014)

Directed, written, co-produced by, and starring Jon Favreau as a chef who, after a public altercation with a food critic, loses his job at a popular Los Angeles restaurant and begins to operate a food truck with his young son. It co-stars Sofía Vergara, John Leguizamo, Scarlett Johansson, Oliver Platt, Bobby Cannavale, and Dustin Hoffman, along with Robert Downey Jr. in a cameo role.

Why it is an Inspirational movie for entrepreneurs: Firstly, the importance of staying true to one’s passion and creative vision, even in the face of resistance and criticism, as demonstrated by Carl Casper’s unwavering dedication to innovative cooking despite clashes with his restaurant’s owner. Secondly, the power of adaptability and resilience in overcoming setbacks and pivoting towards new opportunities is exemplified by Carl’s transformation from a humiliated and unemployed chef to a successful food truck owner and eventually a restaurant entrepreneur. Additionally, the significance of nurturing relationships and leveraging social media for business growth, seen through Percy’s role in promoting the food truck on social platforms, highlights the impact of strong personal and professional networks in entrepreneurship.

Molly’s Game (2017)

Based on the 2014 memoir of the same name by Molly Bloom. The film follows Molly Bloom (Jessica Chastain), who becomes the target of an FBI investigation after the underground poker empire she runs for Hollywood celebrities, athletes, business tycoons, and the Russian mob is exposed.

Why it’s one of the best movies for entrepreneurs: “Molly’s Game” offers valuable lessons about integrity, the importance of ethical decision-making, and the consequences of crossing legal boundaries in the pursuit of wealth and power. Molly’s story serves as a reminder that true success is not measured solely by financial gain, but also by one’s integrity and ability to navigate challenging situations with grace and resilience.

Big Night (1996)

Co-directed by Campbell Scott and Stanley Tucci. Set in the 1950s on the Jersey Shore, the film follows two Italian immigrant brothers, played by Stanley Tucci and Tony Shaloub, as they host an evening of free food at their restaurant in an effort to allow it to gain greater exposure.

Why it’s one of the best movies for entrepreneurs: “Big Night” the importance of staying true to one’s vision and values, even in the face of challenges and setbacks. Primo’s unwavering commitment to authenticity in his culinary craft and Secondo’s resilience in pursuing their entrepreneurial dreams despite obstacles highlight the necessity of passion and dedication in business endeavors.

It’s a Wonderful Life (1946)

Based on the short story and booklet “The Greatest Gift” self-published by Philip Van Doren Stern in 1943, which itself is loosely based on the 1843 Charles Dickens novella A Christmas Carol. The film stars James Stewart as George Bailey, a man who has given up his personal dreams in order to help others in his community and whose thoughts of suicide on Christmas Eve bring about the intervention of his guardian angel, Clarence Odbody. Clarence shows George all the lives he touched and what the world would be like if he had not existed.

Why it’s one of the best movies for entrepreneurs: “It’s a Wonderful Life” underscores the idea that true wealth lies not in material possessions, but in the intangible blessings of love, friendship, and human connection. Through George’s journey, entrepreneurs can be reminded of the importance of prioritizing meaningful relationships and making a positive impact on the lives of others as they pursue their goals and aspirations.

Thank You for Smoking (2005)

Based on the 1994 satirical novel of the same name by Christopher Buckley. It follows the efforts of Big Tobacco’s chief spokesman, Nick Naylor (Aaron Eckhart), who lobbies on behalf of cigarettes using heavy spin tactics while also trying to remain a role model for his 12-year-old son (Cameron Bright).

Why it’s one of the best movies for entrepreneurs: “Thank You for Smoking” serves as a thought-provoking exploration of the complex intersection between business, ethics, and public perception, offering valuable insights for entrepreneurs navigating similar challenges in their own ventures.

Lord of War (2005)

Lord of War follows Yuri Orlov as he enters the illegal arms trade shortly before the dissolution of the Soviet Union, eventually becoming a well-known and unscrupulous gun runner. Directed by Andrew Niccol, starring Nicolas Cage, Jared Leto, Bridget Moynahan, and Ethan Hawke.

Why it’s one of the best movies for entrepreneurs: “Lord of War” serves as a cautionary tale that prompts entrepreneurs to reflect on the ethical, moral, and strategic dimensions of their business decisions, while also highlighting the broader societal implications of their actions.